US6565614B1ExpiredUtilityPatentIndex 93
Cationic oxidation bases, their use for oxidation dyeing of keratin fibres, dyeing compositions and dyeing methods
Est. expiryJul 16, 2017(expired)· nominal 20-yr term from priority
C07C 211/63A61Q 5/10C07C 217/84A61K 8/494A61K 8/416C07D 295/15
93
PatentIndex Score
28
Cited by
49
References
34
Claims
Abstract
The invention relates to novel monobenzene oxidation bases containing at least one cationic group Z bearing at least one quaternary ammonium unit which may or may not be cyclized, to their use for the oxidation dyeing of keratin fibers, to dye compositions containing then and to oxidation dyeing processes using them.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A compound of formula (I), or an acid addition salt thereof:
wherein:
R 1 , R 2 and R 3 , are identical or different and represent
a hydrogen atom;
a halogen atom;
a group Z;
a (C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
a carboxyl radical;
a (C 1 -C 6 )alkylcarboxyl radical;
a C 1 -C 6 alkylsulfonoyl radical;
an aminosulfonyl radical;
an N-Z-aminosulfonyl radical;
a C 1 -C 6 N-alkylaminosulphonyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a carbamyl radical;
an N-(C 1 -C 6 )alkylcarbamyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a cyano radical;
a group OR 6 ;
a group SR 6 ;
an amino group protected with a (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, trifluoro(C 1 -C 6 )alkylcarbonyl, amino(C 1 -C 6 )alkylcarbonyl, N-Z-amino(C 1 -C 6 )alkylcarbonyl, N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, aminosulphonyl, N-Z-aminosulphonyl, C 1 -C 6 N-alkylaminosulphonyl, N,N-di(C 1 -C 6 )alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, (C 1 -C 6 )alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
R 6 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a group Z;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, thiocarbamyl and C 1 -C 6 alkylsulphonyl radicals, and the group Z;
A represents a group —NR 4 R 5 or a hydroxyl radical;
R 4 and R 5 , are identical or different and represent
a hydrogen atom;
a group Z;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a thiocarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a sulpho(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
Z represents a group of formula (II) below:
wherein:
B is a divalent linker arm which represents a linear or branched alkyl chain, said alkyl chain being uninterrupted or interrupted by one or more hetero atoms, and said alkyl chain being unsubstituted or substituted with one or more hydroxyl or C 1 -C 6 alkoxy radicals, and which said chain has no ketone functions or at least one ketone function;
R 7 , R 8 and R 9 , are identical or different and represent
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 -C 6 )alkyl radical,
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical,
a cyano(C 1 -C 6 )alkyl radical,
an aryl radical,
a benzyl radical,
a carbamyl(C 1 -C 6 )alkyl radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical, or
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; or
two of the radicals R 7 , R 8 and R 9 together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered carbon ring, wherein said ring may contain one or more additional hetero atoms, wherein said ring is unsubstituted or substituted with
a halogen atom,
a hydroxyl radical,
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 -C 6 )alkyl radical,
a nitro radical,
a cyano radical,
a cyano(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkoxy radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical,
an amido radical,
an aldehydo radical,
a carboxyl radical,
a (C 1 -C 6 )alkylcarbonyl radical,
a thio radical,
a thio(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkylthio radical,
an amino radical, or
an amino radical protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; and/or
one of R 7 , R 8 and R 9 may represent a second group Z which is identical to or different from the first group Z;
X − represents a monovalent or divalent anion;
R 10 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
an amino(C 1 -C 6 )alkyl radical,
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical;
a sulphonamido(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylketo(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylsulphonamido(C 1 -C 6 )alkyl radical;
x is an integer equal to 0 or 1; with the proviso that:
when x=0, then the divalent linker arm B is attached to the nitrogen atom bearing the radicals R 7 to R 9 ,
when x=1, then two of the radicals R 7 to R 9 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm B is attached to a carbon atom of said saturated ring;
with the proviso that:
the number of cationic groups Z in said compound or acid addition salt thereof is at least equal to 1;
when A represents a group —NR 4 R 5 , and when R 4 or R 5 represents a group Z, and when the divalent linker arm B represents an alkyl chain containing a ketone function, then said ketone function is not directly attached to the nitrogen atom of the group —NR 4 R 5 ;
and further with the proviso that
4-amino-2-fluoro-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-trifluoromethyl-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-cyano-N-(trimethylammonioethyl)aniline iodide;
2-(4-aminophenylamino)ethyltrimethylammonium iodide;
4-amino-3-methyl-N-ethyl-N-(trimethylammonioethyl)aniline chloride;
compounds of formula (I) wherein A is a hydroxyl radical, two of said R 1 , R 2 and R 3 are each a hydrogen atom, the other of said R 1 , R 2 and R 3 is a group Z wherein x=0, B is —CH 2 —, and one and only one of said R 7 , R 8 and R 9 is chosen from 3-hydroxyphenyl radicals and 3-aminophenyl radicals;
compounds of formula (I) wherein R 1 , R 2 and R 3 are each a hydrogen atom, x=0, A is a group —NR 4 R 5 wherein one of said R 4 and R 5 is a hydrogen atom and the other of said R 4 and R 5 is a group Z wherein B is C 1 -C 6 alkyl, one of said R 7 , R 8 and R 9 is chosen from C 1 -C 4 alkyl, monohydroxy (C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxy (C 1 -C 4 )alkyl groups; and the other two of said R 7 , R 8 and R 9 are chosen from C 1 -C 6 alkyl groups;
compounds of formula (I) wherein two of said R 1 , R 2 , and R 3 are each a hydrogen, the other of said R 1 , R 2 , and R 3 is a —CH 3 radical, X − is a bromide anion, A is —NR 4 R 5 , wherein R 4 is a —CH 2 CH 3 radical and R 5 is a Z group, wherein, x=0, B is —C 2 H 4 NHCOCH 2 —, and R 7 , R 8 , and R 9 are each a —CH 2 CH 3 radical;
compounds of formula (I), wherein said R 1 , R 2 , and R 3 are each a hydrogen, X − is a chloride anion, A is —NR 4 R 5 , wherein R 4 is a —CH 2 CH 3 radical and R 5 is a Z group, wherein, x=0, B is —CH 2 CH 2 —, and R 7 , R 8 , and R 9 are each a —CH 3 radical;
and acid addition salts thereof are excluded.
2. A compound of the formula (I) or acid addition salt thereof according to claim 1 , wherein said divalent linker B represents a linear alkyl chain containing from 1 to 14 carbon atoms, or a branched alkyl chain containing from 3 to 14 carbon atoms, and wherein said hetero atoms in said divalent linker B are selected from oxygen, sulphur and nitrogen atoms; and further wherein when two of the radicals R7, R8 and R9 together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring, said ring is selected from a quaternized pyrrolidine, a piperidine, a piperazine, or a morpholine ring.
3. A compound of the formula (I) or acid addition salt thereof according to claim 1 , wherein X − represents a halogen atom, a hydroxide, a hydrogenosulphate, or a C1-C6 alkyl sulphate.
4. A compound of the formula (I) or acid addition salt thereof according to claim 3 , wherein said halogen atom is chlorine, bromine, fluorine or iodine.
5. A compound according to claim 1 , wherein said compound is:
[2-(2,5-diaminophenoxy)ethyl]diethylmethylammonium chloride monohydrate;
N,N-bis(trimethylammoniopropyl)-4-aminoaniline dichloride;
{2-[(4-aminophenyl)methylamino]ethyl}trimethylammonium chloride;
[4-(4-amino-2-methylphenylamino)pentyl]diethylmethylammonium chloride;
[4-(4-amino-3-methylphenylamino)pentyl]diethylmethylammonium chloride;
1-{[5-amino-2-(2-hydroxyethylamino)phenylcarbamoyl]methyl}-1,4-dimethyl-1-piperazinium chloride;
or an acid addition salt thereof.
6. A compound according to claim 5 , wherein said compound is:
[2-(2,5-diaminophenoxy)ethyl]diethylmethylammonium chloride monohydrate;
N,N-bis(trimethylammoniopropyl)-4-aminoaniline chloride;
{2-[(4-aminophenyl)methylamino]ethyl}trimethylammonium chloride;
or an acid addition salt thereof.
7. A method of dyeing keratin fibers comprising applying to said keratin fibers at least one oxidation base selected from compounds of formula (1) and acid addition salts thereof:
wherein:
R 1 , R 2 and R 3 , are identical or different and represent
a hydrogen atom;
a halogen atom;
a group Z;
a (C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
a carboxyl radical;
a (C 1 -C 6 )alkylcarboxyl radical;
a C 1 -C 6 alkylsulphonyl radical;
an aminosulphonyl radical;
an N-Z-aminosulphonyl radical;
a C 1 -C 6 N-alkylaminosulphonyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a carbamyl radical;
an N-(C 1 -C 6 )alkylcarbamyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a cyano radical;
a group OR 6 ;
a group SR 6 ;
an amino group protected with a (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, trifluoro(C 1 -C 6 )alkylcarbonyl, amino(C 1 -C 6 )alkylcarbonyl, N-Z-amino(C 1 -C 6 )alkylcarbonyl, N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, aminosulphonyl, N-Z-aminosulphonyl, C 1 -C 6 N-alkylaminosulphonyl, N,N-di(C 1 -C 6 )alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, (C 1 -C 6 )alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
R 6 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a group Z;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, thiocarbamyl and C 1 -C 6 alkylsulphonyl radicals, and the group Z;
A represents a group —NR 4 R 5 or a hydroxyl radical;
R 4 and R 5 , are identical or different and represent
a hydrogen atom;
a group Z;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a thiocarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a sulpho(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radial;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
Z represents a group of formula (II) below:
wherein:
B is a divalent linker arm which represents a linear or branched alkyl chain, said alkyl chain being uninterrupted or interrupted by one or more hetero atoms, and said alkyl chain being unsubstituted or substituted with one or more hydroxyl or C 1 -C 6 alkoxy radicals, and which said chain has no ketone functions or at least one ketone function;
R 7 , R 8 and R 9 , are identical or different and represent
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 C 6 )alkyl radical,
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical,
a cyano(C 1 -C 6 )alkyl radical,
an aryl radical,
a benzyl radical,
a carbamyl(C 1 -C 6 )alkyl radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical, or
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; or
two of the radicals R 7 , R 8 and R 9 together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered carbon ring, wherein said ring may contain one or more additional hetero atoms, wherein said ring is unsubstituted or substituted with
a halogen atom,
a hydroxyl radical,
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 1 -C 6 )alkyl radical,
a nitro radical,
a cyano radical,
a cyano(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkoxy radical;
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical,
an amido radical,
an aldehydo radical,
a carboxyl radical,
a (C 1 -C 6 )alkylcarbonyl radical,
a thio radical,
a thio(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkylthio radical,
an amino radical, or
an amino radical protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; and/or,
one of R 7 , R 8 and R 9 may represents a second group Z which is identical to or different from the first group Z;
X − represents a monovalent or divalent anion;
R 10 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
an amino(C 1 -C 6 )alkyl radical,
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical,
a sulphonamido(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylketo(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylsulphonamido(C 1 -C 6 )alkyl radical;
x is an integer equal to 0 or 1; with the proviso that:
when x=0, then the divalent linker arm B is attached to the nitrogen atom bearing the radicals R 7 to R 9 ,
when x=1, then two of the radicals R 7 to R 9 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm B is attached to a carbon atom of said saturated ring;
with the proviso that
the number of cationic groups Z in said compound or acid addition salt thereof is at least equal to 1;
when A represents a group —NR 4 R 5 , and when R 4 or R 5 represents a group Z, and when the divalent linker arm B represents an alkyl chain containing a ketone function, then said ketone function is not directly attached to the nitrogen atom of the group —NR 4 R 5 ;
and further with the proviso that
4-amino-2-fluoro-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-trifluoromethyl-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-cyano-N-(trimethylammonioethyl)aniline iodide;
2-(4-aminophenylamino)ethyltrimethylammonium iodide;
4-amino-3-methyl-N-ethyl-N-(trimethylammonioethyl)aniline chloride;
compounds of formula (I) wherein R 1 , R 2 and R 3 are each a hydrogen atom, x=0, A is a group —NR 4 R 5 wherein one of said R 4 and R 5 is a hydrogen atom and the other of said R 4 and R 5 is a group Z wherein B is C 1 -C 6 alkyl, one of said R 7 , R 8 and R 9 is chosen from C 1 -C 4 alkyl, monohydroxy (C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxy (C 1 -C 4 ) alkyl groups; and the other two of said R 7 , R 8 and R 9 are chosen from C 1 -C 6 alkyl groups;
and acid addition salts thereof are excluded.
8. A method according to claim 7 , wherein said keratin fibers are human keratin fibers.
9. A method according to claim 8 , wherein said keratin fibers are hair.
10. A composition for the oxidation dyeing of keratin fibers comprising, in a medium suitable for dyeing, at least one oxidation base selected from the compounds of formula (1) and acid addition salts thereof:
wherein:
R 1 , R 2 and R 3 , are identical or different and represent
a hydrogen atom;
a halogen atom;
a group Z;
a (C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
a carboxyl radical;
a (C 1 -C 6 )alkylcarboxyl radical;
a C 1 -C 6 alkylsulphonyl radical;
an aminosulphonyl radical;
an N-Z-aminosulphonyl radical;
a C 1 -C 6 N-alkylaminosulphonyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a carbamyl radical;
an N-(C 1 -C 6 )alkylcarbamyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a cyano radical;
a group OR 6 ;
a group SR 6 ;
an amino group protected with a (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, trifluoro(C 1 -C 6 )alkylcarbonyl, amino(C 1 -C 6 )alkylcarbonyl, N-Z-amino(C 1 -C 6 )alkylcarbonyl, N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, aminosulphonyl, N-Z-aminosulphonyl, C 1 -C 6 N-alkylaminosulphonyl, N,N-di(C 1 -C 6 )alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, (C 1 -C 6 )alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
R 6 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a group Z;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, thiocarbamyl and C 1 -C 6 alkylsulphonyl radicals, and the group Z;
A represents a group —NR 4 R 5 or a hydroxyl radical;
R 4 and R 5 , are identical or different and represent
a hydrogen atom;
a group Z;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a thiocarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a sulpho(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
Z represents a group of formula (II) below:
wherein:
B is a divalent linker arm which represents a linear or branched alkyl chain, said alkyl chain being uninterrupted or interrupted by one or more hetero atoms, and said alkyl chain being unsubstituted or substituted with one or more hydroxyl or C 1 -C 6 alkoxy radicals, and which said chain has no ketone functions or at least one ketone function;
R 7 , R 8 and R 9 , are identical or different and represent
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 -C 6 )alkyl radical,
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical,
a cyano(C 1 -C 6 )alkyl radical,
an aryl radical,
a benzyl radical,
a carbamyl(C 1 -C 6 )alkyl radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical, or
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; or
two of the radicals R 7 , R 8 and R 9 together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered carbon ring, wherein said ring may contain one or more additional hetero atoms, wherein said ring is unsubstituted or substituted with
a halogen atom,
a hydroxyl radical,
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 -C 6 )alkyl radical,
a nitro radical,
a cyano radical,
a cyano(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkoxy radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical,
an amido radical,
an aldehydo radical,
a carboxyl radical,
a (C 1 -C 6 )alkylcarbonyl radical,
a thio radical,
a thio(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkylthio radical,
an amino radical, or
an amino radical protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; and/or
one of R 7 , R 8 and R 9 may represents a second group Z which is identical to or different from the first group Z;
X − represents a monovalent or divalent anion;
R 10 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
an amino(C 1 -C 6 )alkyl radical,
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical;
a sulphonamido(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylketo(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylsulphonamido(C 1 -C 6 )alkyl radical;
x is an integer equal to 0 or 1; with the proviso that:
when x=0, then the divalent linker arm B is attached to the nitrogen atom bearing the radicals R 7 to R 9 ,
when x=1, then two of the radicals R 7 to R 9 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm B is attached to a carbon atom of said saturated ring;
with the proviso that:
the number of cationic groups Z in said compound or acid addition salt thereof is at least equal to 1;
when A represents a group —NR 4 R 5 , and when R 4 or R 5 represents a group Z, and when the divalent linker arm B represents an alkyl chain containing a ketone function, then said ketone function is not directly attached to the nitrogen atom of the group —NR 4 R 5 ;
and further with the proviso that
4-amino-2-fluoro-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-trifluoromethyl-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-cyano-N-(trimethylammonioethyl)aniline iodide;
2-(4-aminophenylamino)ethyltrimethylammonium iodide;
4-amino-3-methyl-N-ethyl-N-(trimethylammonioethyl)aniline chloride;
compounds of formula (I) wherein A is a hydroxyl radical, two of said R 1 , R 2 and R 3 are each a hydrogen atom, the other of said R 1 , R 2 and R 3 is a group Z wherein x=0, B is —CH 2 —, and one and only one of said R 7 , R 8 and R 9 is chosen from 3-hydroxyphenyl radicals and 3-aminophenyl radicals;
compounds of formula (I) wherein R 1 , R 2 and R 3 are each a hydrogen atom, x=0, A is a group —NR 4 R 5 wherein one of said R 4 and R 5 is a hydrogen atom and the other of said R 4 and R 5 is a group Z wherein B is C 1 -C 6 alkyl, one of said R 7 , R 8 and R 9 is chosen from C 1 -C 4 alkyl, monohydroxy (C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxy (C 1 -C 4 )alkyl groups; and the other two of said R 7 , R 8 and R 9 are chosen from C 1 -C 6 alkyl groups;
and acid addition salts thereof are excluded.
11. A composition according to claim 10 , wherein said keratin fibers are human keratin fibers.
12. A composition according to claim 11 , wherein said human keratin fibers are hair.
13. A composition according to claim 10 , wherein said at least one oxidation base is present in an amount ranging from 0.0005 to 12% by weight relative to the total weight of said composition.
14. A composition according to claim 13 , wherein said at least one oxidation base is present in an amount ranging from 0.005 to 6% by weight relative to the total weight of said composition.
15. A composition according to claim 10 , wherein said medium suitable for dyeing comprises water or a mixture of water and at least one organic solvent selected from C1-C4 lower alkanols, glycerol, glycols and glycol ethers, or aromatic alcohols.
16. A composition according to claim 15 , wherein said at least one organic solvent is selected from ethanol, isopropanol, 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, diethylene glycol monoethyl ether and monomethyl ether, benzyl alcohol, and phenoxyethanol.
17. A composition according to claim 10 , having a pH ranging from about 3 to 12.
18. A composition according to claim 17 , having a pH ranging from about 5 to about 11.
19. A composition according to claim 10 , further comprising at least one additional oxidation base selected from para-phenylenediamines other than said at least one compound of formula (I), bis(phenyl)alkylenediamines, para-aminophenols other than said at least one compound of formula (I), ortho-aminophenols and heterocyclic bases.
20. A composition according to claim 19 , wherein said at least one addtional oxidation base is selected from para-phenylenediamine, para-toluylenediamine, 2,6-dimethyl-para-phenylenediamine, 2-β-hydroxyethyl-para-phenylenediamine, 2-n-propyl-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(β-hydroxypropyl)-para-phenylenediamine, N,N-bis(β-hydroxyethyl)-para-phenylenediamine, 4-amino-N-(β-methoxyethyl)aniline, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)-1,3-diaminopropanol, N,N′-bis(β13-hydroxyethyl)-N,N′-bis(4-aminophenyl)ethylenediamine, N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(4-methylaminophenyl)tetramethylenediamine, N,N′-bis(ethyl)-N,N′-bis(4-amino-3-methylphenyl)ethylenediamine, para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(-hydroxyethylaminomethyl)phenol, 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, pyridine derivatives, pyrimidine derivatives, and pyrazole derivatives.
21. A composition according to claim 19 , wherein said at least one additional oxidation base is present in an amount ranging from 0.0005 to 12% by weight relative to the total weight of said composition.
22. A composition according to claim 21 , wherein said at least one additional oxidation base is present in amount ranging from 0.005 to 6% by weight relative to the total weight of said composition.
23. A composition according to claim 10 , further comprising at least one coupler and/or at least one direct dye.
24. A composition according to claim 23 , wherein said at least one coupler is selected from meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers, and acid addition salts thereof.
25. A composition according to claim 24 , wherein said at least one coupler is selected from indole derivatives, indolene derivatives, pyridine derivatives, pyrazolones, 2-methyl-5-aminophenol, 5-N-(β-hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene, 2,4-diamino-1-(β-hydroxyethyloxy)benzene, 2-amino-4-(β-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, α-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxyindoline, 6-hydroxybenzomorpholine, 2,6-dihydroxy-4-methylpyridine, 1H-3-methylpyrazol-5-one, and 1-phenyl-3-methylpyrazol-5-one.
26. A composition according to claim 23 , wherein said at least one coupler is present in an amount ranging from 0.0001 to 10% by weight relative to the total weight of said composition.
27. A composition according to claim 26 , wherein said at least one coupler is present in an amount ranging from 0.005 to 5% by weight relative to the total weight of said composition.
28. A composition according to claim 10 , wherein said acid addition salt is selected from hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates.
29. A composition according to claim 10 , wherein said composition is in the form of a liquid, a gel, or a cream.
30. A method for dyeing keratin fibers, comprising the steps of: applying a composition for the oxidation dyeing of keratin fibers comprising, in a medium suitable for dyeing, at least one oxidation base selected from the compounds of formula (1) and acid addition salts thereof:
wherein:
R 1 , R 2 and R 3 , are identical or different and represent
a hydrogen atom;
a halogen atom;
a group Z;
a (C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
a carboxyl radical;
a (C 1 -C 6 )alkylcarboxyl radical;
a C 1 -C 6 alkylsulphonyl radical;
an aminosulphonyl radical;
an N-Z-aminosulphonyl radical;
a C 1 -C 6 N-alkylaminosulphonyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a carbamyl radical;
an N-(C 1 -C 6 )alkylcarbamyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a cyano radical;
a group OR 6 ;
a group SR 6 ;
an amino group protected with a (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, trifluoro(C 1 -C 6 )alkylcarbonyl, amino(C 1 -C 6 )alkylcarbonyl, N-Z-amino(C 1 -C 6 )alkylcarbonyl, N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, aminosulphonyl, N-Z-aminosulphonyl, C 1 -C 6 N-alkylaminosulphonyl, N,N-di(C 1 -C 6 )alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, (C 1 -C 6 )alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
R 6 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a group Z;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, thiocarbamyl and C 1 -C 6 alkylsulphonyl radicals, and the group Z;
A represents a group —NR 4 R 5 or a hydroxyl radical;
R 4 and R 5 , are identical or different and represent
a hydrogen atom;
a group Z;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a thiocarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a sulpho(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
Z represents a group of formula (II) below:
wherein:
B is a divalent linker arm which represents a linear or branched alkyl chain, said alkyl chain being uninterrupted or interrupted by one or more hetero atoms, and said alkyl chain being unsubstituted or substituted with one or more hydroxyl or C 1 -C 6 alkoxy radicals, and which said chain has no ketone functions or at least one ketone function;
R 7 , R 8 and R 9 , are identical or different and represent
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 -C 6 )alkyl radical,
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical,
a cyano(C 1 -C 6 )alkyl radical,
an aryl radical,
a benzyl radical,
a carbamyl(C 1 -C 6 )alkyl radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical, or
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; or
two of the radicals R 7 , R 8 and R 9 together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered carbon ring, wherein said ring may contain one or more additional hetero atoms, wherein said ring is unsubstituted or substituted with
a halogen atom,
a hydroxyl radical,
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 -C 6 )alkyl radical,
a nitro radical,
a cyano radical,
a cyano(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkoxy radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical,
an amido radical,
an aldehydo radical,
a carboxyl radical,
a (C 1 -C 6 )alkylcarbonyl radical,
a thio radical,
a thio(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkylthio radical,
an amino radical, or
an amino radical protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; and/or
one of R 7 , R 8 and R 9 may represents a second group Z which is identical to or different from the first group Z;
X − represents a monovalent or divalent anion;
R 10 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
an amino(C 1 -C 6 )alkyl radical,
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical;
a sulphonamido(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylketo(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylsulphonamido(C 1 -C 6 )alkyl radical;
x is an integer equal to 0 or 1; with the proviso that:
when x=0, then the divalent linker arm B is attached to the nitrogen atom bearing the radicals R 7 to R 9 ,
when x=1, then two of the radicals R 7 to R 9 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm B is attached to a carbon atom of said saturated ring;
with the proviso that:
the number of cationic groups Z in said compound or acid addition salt thereof is at least equal to 1;
when A represents a group —NR 4 R 5 , and when R 4 or R 5 represents a group Z, and when the divalent linker arm B represents an alkyl chain containing a ketone function, then said ketone function is not directly attached to the nitrogen atom of the group —NR 4 R 5 ;
and further with the proviso that
4-amino-2-fluoro-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-trifluoromethyl-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-cyano-N-(trimethylammonioethyl)aniline iodide;
2-(4-aminophenylamino)ethyltrimethylammonium iodide;
4-amino-3-methyl-N-ethyl-N-(trimethylammonioethyl)aniline chloride;
compounds of formula (I) wherein A is a hydroxyl radical, two of said R 1 , R 2 and R 3 are each a hydrogen atom, the other of said R 1 , R 2 and R 3 is a group Z wherein x=0, B is —CH 2 —, and one and only one of said R 7 , R 8 and R 9 is chosen from 3-hydroxyphenyl radicals and 3-aminophenyl radicals;
compounds of formula (I) wherein R 1 , R 2 and R 3 are each a hydrogen atom, x=0, A is a group —NR 4 R 5 wherein one of said R 4 and R 5 is a hydrogen atom and the other of said R 4 and R 5 is a group Z wherein B is C 1 -C 6 alkyl, one of said R 7 , R 8 and R 9 is chosen from C 1 -C 4 alkyl, monohydroxy (C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxy (C 1 -C 4 )alkyl groups; and the other two of said R 7 , R 8 and R 9 are chosen from C 1 -C 6 alkyl groups;
and acid addition salts thereof are excluded to said keratin fibers and developing color in acidic, neutral or alkaline pH using an oxidizing agent, wherein said oxidizing agent is either added to said oxidizing composition at the time of applying to said fibers, or is present in an oxidizing composition which is applied simultaneously or sequentially with said composition.
31. A method according to claim 30 , wherein said oxidizing agent is selected from hydrogen peroxide, urea peroxide, alkali metal bromates and persalts.
32. A method according to claim 31 , wherein said oxidizing agent is selected from perborates and persulphates.
33. A method according to claim 31 , wherein said oxidizing agent is hydrogen peroxide.
34. A multi-component dyeing device or kit for dyeing keratin fibers comprising at least two compartments, wherein,
a first compartment comprises a composition for the oxidation dyeing of keratin fibers comprising, in a medium suitable for dyeing, at least one oxidation base selected from the compounds of formula (1) and acid addition salts thereof:
wherein:
R 1 , R 2 and R 3 , are identical or different and represent
a hydrogen atom;
a halogen atom;
a group Z;
a (C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl radical;
an amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-Z-amino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
a carboxyl radical;
a (C 1 -C 6 )alkylcarboxyl radical;
a C 1 -C 6 alkylsulphonyl radical;
an aminosulphonyl radical;
an N-Z-aminosulphonyl radical;
a C 1 -C 6 N-alkylaminosulphonyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a carbamyl radical;
an N-(C 1 -C 6 )alkylcarbamyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a cyano radical;
a group OR 6 ;
a group SR 6 ;
an amino group protected with a (C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, trifluoro(C 1 -C 6 )alkylcarbonyl, amino(C 1 -C 6 )alkylcarbonyl, N-Z-amino(C 1 -C 6 )alkylcarbonyl, N-(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, N,N-di(C 1 -C 6 )alkylamino(C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, aminosulphonyl, N-Z-aminosulphonyl, C 1 -C 6 N-alkylaminosulphonyl, N,N-di(C 1 -C 6 )alkylaminosulphonyl, thiocarbamyl or formyl radical, or with a group Z;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, (C 1 -C 6 )alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
R 6 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a group Z;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, thiocarbamyl and C 1 -C 6 alkylsulphonyl radicals, and the group Z;
A represents a group —NR 4 R 5 or a hydroxyl radical;
R 4 and R 5 , are identical or different and represent
a hydrogen atom;
a group Z;
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
a thiocarbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a sulpho(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
an aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-Z-aminosulphonyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
an N,N-di(C 1 -C 6 )alkylaminosulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarbonyl(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical;
an amino(C 1 -C 6 )alkyl radical wherein the amine is substituted with one or two identical or different radicals selected from C 1 -C 6 alkyl, monohydroxy(C 1 -C 6 )alkyl, polyhydroxy(C 1 -C 6 )alkyl, (C 1 -C 6 )alkylcarbonyl, carbamyl, N-(C 1 -C 6 )alkylcarbamyl, N,N-di(C 1 -C 6 )alkylcarbamyl, C 1 -C 6 alkylsulphonyl, formyl, trifluoro(C 1 -C 6 )alkylcarbonyl, (C 1 -C 6 )alkylcarboxyl and thiocarbamyl radicals, or with a group Z;
Z represents a group of formula (II) below:
wherein:
B is a divalent linker arm which represents a linear or branched alkyl chain, said alkyl chain being uninterrupted or interrupted by one or more hetero atoms, and said alkyl chain being unsubstituted or substituted with one or more hydroxyl or C 1 -C 6 alkoxy radicals, and which said chain has no ketone functions or at least one ketone function;
R 7 , R 8 and R 9 , are identical or different and represent
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 -C 6 )alkyl radical,
a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl radical,
a cyano(C 1 -C 6 )alkyl radical,
an aryl radical,
a benzyl radical,
a carbamyl(C 1 -C 6 )alkyl radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical, or
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; or
two of the radicals R 7 , R 8 and R 9 together form, with the nitrogen atom to which they are attached, a saturated 5- or 6-membered carbon ring, wherein said ring may contain one or more additional hetero atoms, wherein said ring is unsubstituted or substituted with
a halogen atom,
a hydroxyl radical,
a C 1 -C 6 alkyl radical,
a monohydroxy(C 1 -C 6 )alkyl radical,
a polyhydroxy(C 2 -C 6 )alkyl radical,
a nitro radical,
a cyano radical,
a cyano(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkoxy radical,
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical,
an amido radical,
an aldehydo radical,
a carboxyl radical,
a (C 1 -C 6 )alkylcarbonyl radical,
a thio radical,
a thio(C 1 -C 6 )alkyl radical,
a C 1 -C 6 alkylthio radical,
an amino radical, or
an amino radical protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical; and/or
one of R 7 , R 8 and R 9 may represents a second group Z which is identical to or different from the first group Z;
X − represents a monovalent or divalent anion;
R 10 represents
a C 1 -C 6 alkyl radical;
a monohydroxy(C 1 -C 6 )alkyl radical;
a polyhydroxy(C 2 -C 6 )alkyl radical;
an aryl radical;
a benzyl radical;
an amino(C 1 -C 6 )alkyl radical,
an amino(C 1 -C 6 )alkyl radical wherein the amine is protected with a (C 1 -C 6 )alkylcarbonyl, carbamyl or C 1 -C 6 alkylsulphonyl radical;
a carboxy(C 1 -C 6 )alkyl radical;
a cyano(C 1 -C 6 )alkyl radical;
a carbamyl(C 1 -C 6 )alkyl radical;
a trifluoro(C 1 -C 6 )alkyl radical;
a tri(C 1 -C 6 )alkylsilane(C 1 -C 6 )alkyl radical;
a sulphonamido(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylcarboxy(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphinyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylsulphonyl(C 1 -C 6 )alkyl radical;
a (C 1 -C 6 )alkylketo(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylcarbamyl(C 1 -C 6 )alkyl radical;
an N-(C 1 -C 6 )alkylsulphonamido(C 1 -C 6 )alkyl radical;
x is an integer equal to 0 or 1; with the proviso that:
when x=0, then the divalent linker arm B is attached to the nitrogen atom bearing the radicals R 7 to R 9 ,
when x=1, then two of the radicals R 7 to R 9 form, together with the nitrogen atom to which they are attached, a saturated 5- or 6-membered ring as defined above, and the linker arm B is attached to a carbon atom of said saturated ring;
with the proviso that:
the number of cationic groups Z in said compound or acid addition salt thereof is at least equal to 1;
when A represents a group —NR 4 R 5 , and when R 4 or R 5 represents a group Z, and when the divalent linker arm B represents an alkyl chain containing a ketone function, then said ketone function is not directly attached to the nitrogen atom of the group —NR 4 R 5 ;
and further with the proviso that
4-amino-2-fluoro-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-trifluoromethyl-N-(trimethylammonioethyl)aniline iodide;
4-amino-2-cyano-N-(trimethylammonioethyl)aniline iodide;
2-(4-aminophenylamino)ethyltrimethylammonium iodide;
4-amino-3-methyl-N-ethyl-N-(trimethylammonioethyl)aniline chloride;
compounds of formula (I) wherein A is a hydroxyl radical, two of said R 1 , R 2 and R 3 are each a hydrogen atom, the other of said R 1 , R 2 and R 3 is a group Z wherein x=0, B is —CH 2 —, and one and only one of said R 7 , R 8 and R 9 is chosen from 3-hydroxyphenyl radicals and 3-aminophenyl radicals;
compounds of formula (I) wherein R 1 , R 2 and R 3 are each a hydrogen atom, x=0, A is a group —NR 4 R 5 wherein one of said R 4 and R 5 is a hydrogen atom and the other of said R 4 and R 5 is a group Z wherein B is C 1 -C 6 alkyl, one of said R 7 , R 8 and R 9 is chosen from C 1 -C 4 alkyl, monohydroxy (C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxy (C 1 -C 4 )alkyl groups; and the other two of said R 7 , R 8 and R 9 are chosen from C 1 -C 6 alkyl groups;
and acid addition salts thereof are excluded and
a second compartment comprises an oxidizing composition.Cited by (0)
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